Sodium Hydroxide → N-o-Tolyl-3-(trifluoromethyl)-1H-pyrrole-2-carboxamide

HRID 524982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 524982
C1(S([N:10]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[C:11]2[C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])=[O:20])(=O)=O)C=CC=CC=1.[OH-].[Na+]>CO>[C:23]1([CH3:28])[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:21][C:19]([C:11]1[NH:10][CH:14]=[CH:13][C:12]=1[C:15]([F:16])([F:17])[F:18])=[O:20]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 709223191-(Phenylsulfonyl)-N-o-tolyl-3-(trifluoromethyl)-1H-pyrrole-2-carboxamide

Produkt 1

HCID 70922391N-o-Tolyl-3-(trifluoromethyl)-1H-pyrrole-2-carboxamideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-(phenylsulfonyl)-N-o-tolyl-3-(trifluoromethyl)-1H-pyrrole-2-carboxamide (560 mg of crude material) in 12 mL of methanol was added 2 mL of an aqueous 1N solution of sodium hydroxide and the mixture was stirred at room temperature during 1 h. At the end of this period, no starting material was detected and the reaction was elaborated in the following way: methanol was evaporated and water was added basifying the mixture with saturated aqueous solution of potassium carbonate. This mixture was extracted with ethyl acetate and this organic phase was washed with water and brine, dried (Na2SO4) and concentrated to dryness affording a reddish residue. This residue was purified by flash chromatography silica (hexane/ethyl ether). Concentration of the fractions containing the compound afforded 120 mg (50%) of the title compound.

Aufarbeitung

  1. custommethanol was evaporated
  2. additionwater was added basifying the mixture with saturated aqueous solution of potassium carbonate
  3. extractionThis mixture was extracted with ethyl acetate
  4. washthis organic phase was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness
  7. customaffording a reddish residue
  8. customThis residue was purified by flash chromatography silica (hexane/ethyl ether)
  9. additionConcentration of the fractions containing the compound

Quellen und Nachweise

ORD-Eintrag
ord-e065a7509ca44cf4b2e62554317bdcbc
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340547B2

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